Day Trips
Mountain Biking in Stillwell

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Awesome single-track course for bikers with experience!

Killer riding on single-track course in Stillwell, Long Island—10 to 12 miles! You can take it fast and hard, or slow and sure through twists and turns, undulating hills, occasional rocks and conspiring roots.

Two top, experienced Outdoor Bound guides will lead you and instruct according to your needs. This is a great trail—one of our favorites. You’ll learn bunny hops, how to go over logs and other obstacles, work with steep and rocky terrain, learn about distribution of weight and much more. The course will be varied between 10-mile or 16-mile trails, depending on comfort level and ability. We will also break throughout the day as needed.

Two licensed guides and insurance included. Train tickets are out-of-pocket (about $19, purchase at the train station). You may also drive to meet us at the Cold Spring Harbor (Long Island) train station.

Bike Requirements

  • It must be a mountain bike!
  • Must have knobby mountain bike tires
  • Brakes need to be in good working order
  • Front suspension (shocks) recommended but not required
  • Helmet required; eye protection recommended
  • Spare tire tube recommended

If your bike does not meet the above requirements, you may be required to rent a bike in advance of the trip. This is to ensure your safety as well as the compatibility of all riders.

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Bike Rental

You must bring a bike and helmet on this trip. If you don’t own a bike, you may rent one from area bike stores. One we can recommend:

Manhattan Bicycle
791 Ninth Avenue
New York, New York
Open 10 AM - 7 PM
Phone: (212) 262-0111
You will need to do an overnight rental (pick bike up the evening before the trip).

Helmets are required for all riders; you must provide your own.

Event Details

  • Trip Includes Experienced biking guides, insurance and unlimited fun
  • Leave Penn Station, LIRR, Port Jefferson Line. Depart @ 8:24 AM, arrive Syosset 9:16 AM. Our guides will meet you at the Syosset station.
  • Return LIRR Train departs Syosset at 1:14 PM and 1:46 PM. You are welcome to bike for additional time, but it will be at your own risk, as a guide will not be present.
  • Train Tickets Out-of-pocket (about $16)—purchase at Penn Station. Tickets are $7.75 each way--buy ticket at the station (not on the train).
  • Drive to Meet Us You may meet us at the Syosset train station; please arrive by 9:15 AM.

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16 to 23 Miles of Great Riding

The 10-15 miles of moderate to challenging single-track riding is intended for bikers with intermediate to advanced riding ability. Our modified, shorter rides (10 or 16 miles) are intended for the experienced beginner-to-intermediate rider who is looking to learn some new skills such as efficient shifting, cadence, bunny-hops, riding over logs, and climbing and descending hills. The trail provides for advanced hill climbs and steep technical descents.

The hard-pack greenbelt single-track is well maintained and makes for a challenging ride with a number of decent climbs and descents but not too much technical difficulty. Once in the woods, the trail unravels from an abandoned farm field to a deep forest of many twists, turns, miniature loops and hilly terrain. Good bike-handling skills are necessary to negotiate the many tight corners. This trail was designed and built specifically to take advantage of the varied hilly terrain, and the amount of vertical feet gained in this ride accumulates rapidly.

Intensity Levels

This event or trip is Intensity Level 3.

Riders need to have some experience (not suitable for absolute beginners) and be comfortable on a bike. If you have ridden a mountain bike one or two times and liked it, you will enjoy this trip. We will stop and rest as necessary.

Overview > Adventures at All Skill Levels

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We offer adventures for everyone, no matter what your skill level. This guide will help you decide which trip is right for you.

  1. Activity

    How long (in hours) you may be active every day during the trip.

  2. Distances

    You should feel confident that you would be able to complete these distances every day of your trip.

  3. Surfaces

    What types of terrain you may encounter and should be prepared for on your trip.

  4. Elevation Change

    The largest elevation change you may encounter on your trip.

  5. Altitude

    The highest elevation you may reach on your trip.

Level 1 > Laid-Back, Unhurried, Restful

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  1. Activity

    1 – 3 hours

  2. Distances

    Walk or hike less than 3 miles

  3. Surfaces

    Flat terrain

  4. Elevation Change

    Little or none

  5. Altitude

    Less than 3,000 feet

Level 2 > Easy Active — Perfect for Active First-Timers

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  1. Activity

    2 – 5 hours

  2. Distances

    Hike up to 6 miles, cycle 10 – 30 miles most days

  3. Surfaces

    Flat or rolling terrain with some steeps possible

  4. Elevation Change

    Up to 1,500 feet per day

  5. Altitude

    Up to 6,000 feet

Level 3 > Moderate — for Novices & Above

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  1. Activity

    4 – 6 hours most days

  2. Distances

    Hike up to 10 miles, cycle 20 – 40 miles most days

  3. Surfaces

    Rolling or mountainous terrain with some steeps

  4. Elevation Change

    Up to 2,000 feet per day

  5. Altitude

    Up to 10,000 feet

Level 4 > Vigorous — Recommended for Fit Travelers with Basic Skills

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Experience required.

  1. Activity

    5 – 8 hours most days

  2. Distances

    Hike up to 12 miles, cycle 30 – 50 miles most days

  3. Surfaces

    Mountainous, exposed terrain with steep ascents/descents and uneven trails

  4. Elevation Change

    Up to 3,000 feet per day

  5. Altitude

    Up to 14,000 feet

Level 5 > Strenuous — Very Fit or Experienced Travelers

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Experience required; doctor’s release may be required (if so, will be noted in trip description).

  1. Activity

    10 plus hours per day

  2. Distances

    Hike 12 or more miles, cycle 50 miles most days

  3. Surfaces

    Remote mountainous, exposed terrain with steep ascent and descents, uneven trails with loose features

  4. Elevation Change

    Up to 4,000+ feet per day

  5. Altitude

    May well exceed 14,000 feet

Outdoor Bound Winter Hike & Hound Eight Mile Hike

Winter Hike & Hound Eight Mile Hike

Experienced, Fun & Qualified Guides

From cycling across the United States to leading horse treks through New Zealand to scaling Nepalese peaks, Outdoor Bound guides have real-world outdoor experience. Collectively, they have hiked, biked, climbed and kayaked tens of thousands of miles around the globe.

Whether their professional backgrounds are as teachers, personal trainers, artists, environmentalists or business leaders, they all have an extensive knowledge of the natural world and local history. Each guide has also passed a rigorous guide certification program and is trained in wilderness first aid or as a Wilderness First Responder.

Diverse & Interesting Groups

There is no typical Outdoor Bound participant. While ages typically range from 20 to 50, those who come to experience outdoor adventure range from singles to couples, from lawyers to waiters. They are a mix of women and men. While the group is always diverse, you will certainly feel welcome. Our guides go the extra mile to make the atmosphere of each trip social and fun. Many people in the Outdoor Bound community have forged lasting friendships as a result of our trips.

New Experiences

Skydiving, ice-climbing, hot-air ballooning, skiing and hiking every weekend are just a few of Outdoor Bound’s year-round adventures. These trips are accessible to everyone, including the novice, who might feel a little uneasy, the young urban professional trying to get away and even the adrenaline junkie looking for a new rush.

Environmental Awareness

“Leave nothing but footprints, take nothing but pictures,” is the Leave No Trace motto embraced by Outdoor Bound. From purchasing bamboo T-shirts to printing with soy-based inks on recycled paper, Outdoor Bound strives to create the least environmental impact possible while on trips and in the office.

Outdoor Bound Singles Schunemunk Mountain Hike

Singles Schunemunk Mountain Hike

Other Trips in This Category

  1. 3rd of July Hike & Swim
  2. 4th of July Hike & Swim
  3. Adventure Tri Clinic
  4. Autumn Glider Soaring
  5. Autumn Mohonk Scramble Challenge
  6. Autumn Waterfall Canyoneering
  7. Awosting Falls
  8. Backcountry Snowshoe on Russian Bear Mountain
  9. Backwoods Snow Sledding
  10. Backwoods Snowshoeing
  11. Backwoods Snowshoeing: Catskill Mountains, High Point
  12. Backwoods Snowshoeing: Catskills, Panther Mountain
  13. Backwoods Snowshoeing: Catskills, Slide Mountain
  14. Backwoods Snowshoeing: Surebridge Mountain
  15. Bearfort Mountain Hike
  16. Black Ash Mountain Hike
  17. Black Rock Hike
  18. Breakneck Ridge Hike & Scramble
  19. Breakneck Ridge Hike to Mount Taurus
  20. Bullets, Beer & BBQ
  21. Canoe & Kayak
  22. Canopus Lake Hike
  23. Castle Ruin Hike
  24. Catskills Hike & Rappel: Panther Mountain
  25. Catskills Hike: Indian Head Mountain
  26. Catskills Hike: Panther Mountain
  27. Catskills Hike: Slide Mountain
  28. Catskills Hike: Sugarloaf Mountain
  29. Catskills Snowshoeing & Rappelling
  30. Class V Whitewater Rafting
  31. Clay’s Private Rock Climbing, Hiking & Camping Weekend
  32. Columbus Day 6 Mile Hike: Gertrude’s Nose in Minnewaska
  33. Cross Country Ski & Snowshoe
  34. Diamond Mountain Hike
  35. Dog, Beach & Vine
  36. Echo Lake Hike
  37. Empire Hotel Rooftop Cocktails & Gear Raffle
  38. End to End: Sterling Ridge Hike
  39. Evening Horseback, Hayride & Cookout
  40. Fall Foliage Hike, Apple & Pumpkin Picking
  41. Fall Foliage Horseback, Apple & Pumpkin Picking
  42. Fourteen Peaks Hike
  43. Fourth of July Skydiving!
  44. Full Moon Halloween Hike
  45. Full Moon Hike
  46. Full Moon Kayaking to Abandoned Castle
  47. Gertrude’s Nose 6 Mile Hike in Minnewaska
  48. Groundhog Day Hike: Russian Bear
  49. Gunks Hike & Whiskey Tasting
  50. Gunks Horseback Riding & Whiskey Tasting
  51. Gunks Winter Hike & Whiskey Tasting
  52. Half Day Hudson Valley Biking, Hiking & Pub
  53. Halloween Costume Hike & Pub
  54. Halloween Hangover Hike: Ramapo Ridge 9 Miles
  55. Halloween Horseback Riding & Wine Tasting
  56. Hang Gliding Adventure
  57. High Peterskill Hike in Minnewaska
  58. High Ridge Hike & Yoga
  59. High Ropes Climbing
  60. Hike & Art Gallery
  61. Hike & Hound 6-Mile Hike
  62. Hike & Hound Eight Mile Hike
  63. Hike & Pilates
  64. Hike & Wine Tasting
  65. Hike The Great Escape
  66. Hike the Hamptons
  67. Hike to High Point in the Catskills Mountains
  68. Hike, Swim & Wine Tasting
  69. Hike, Swim, Wine Tasting & Grateful Dead Tribute
  70. Hike, Swim, Wine Tasting & Harvest Moon Folk Festival
  71. Hike, Swim, Wine Tasting & Johnny Cash Tribute
  72. Hike, Wine & Charcuterie Tasting
  73. Hike, Wine & Fondue Dinner: Appalachian Trail
  74. Hike, Wine & Fondue Dinner: Ship Rock Ridge
  75. Hike, Wine & Fondue Dinner: Tom Jones Mountain
  76. Hike, Wine & Fondue Tasting: Tom Jones Mountain
  77. Hike, Wine & Shakespeare in the Orchard
  78. Hike, Yoga & Swim
  79. Hippo Rock Hike
  80. Hollywood Stunt Class: High Falls
  81. Hollywood Stunt Class: Trampoline
  82. Horseback & Art Gallery
  83. Horseback & Hike
  84. Horseback Riding & Wine Tasting
  85. Horseback Riding and Introduction to Polo
  86. Horseback, Hike & Swim
  87. Horseback, Wine Tasting & Apple Picking
  88. Hot Air Ballooning
  89. Hudson Half Day Sailing & Hike
  90. Hudson River Brunch Sailing Excursion
  91. Hudson River Sunset Sea Kayaking Intro & Pub
  92. Hudson Sailing & Hike
  93. Hudson Valley Biking, Hiking & Pub
  94. Ice Climbing
  95. Indoor Rock & Pints
  96. Indoor Rock Climbing
  97. Intro to Dragon Boat Racing
  98. Iron Mine & Lemon Squeezer Hike
  99. Kaaterskill Falls Eight Mile Hike
  100. Kristin’s Private Hike, Wine & Fondue Tasting

Bringing a Friend or Two?

Please be sure to enter the total number of people in the Qty box. In addition, be sure to include your friends’ names and cell-phone numbers on the final Checkout page. The final discount price is the price per person, multiplied by the Qty you enter.

Reminder about Trip Conditions

We closely monitor snow, ice and related weather conditions before each trip. Lack of snow or similar, unsatisfactory weather/trail/river conditions may lead to changes to the trip or rescheduling or cancellation.

Please consult the individual trip description or Event Calendar for notice of any such changes. Refer to our full Policies page for more information about reservations and cancellations.

Register > Mountain Biking in Stillwell

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